1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-Amino-N-(2-chloroethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamide

HRID 1693277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693277
[NH2:1][C:2]1[N:3]=[C:4]2[C:13]3[C:7]([CH2:8][CH:9]([C:14]([OH:16])=O)[S:10][C:11]=3[N:12]=1)=[N:6][N:5]2[CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=1.Cl.[Cl:29][CH2:30][CH2:31][NH2:32].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(N(CC)CC)C>[NH2:1][C:2]1[N:3]=[C:4]2[C:13]3[C:7]([CH2:8][CH:9]([C:14]([NH:32][CH2:31][CH2:30][Cl:29])=[O:16])[S:10][C:11]=3[N:12]=1)=[N:6][N:5]2[CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=1

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 97937372-Chloroethylamine hydrochlorideHCID 444763184-amino-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxylic acid

Produkt 1

HCID 593114214-Amino-N-(2-chloroethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture composed of 4-amino-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxylic acid of Example 8 (40 mg), 2-chloroethylamine hydrochloride (24 mg), 1-hydroxybenzotriazole monohydrate (24 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (40 mg), triethylamine (44 μL) and dehydrated N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate and sequentially washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (dichloromethane-ethyl acetate) to obtain the title compound (10 mg, 22%) as a solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with ethyl acetate
  3. washsequentially washed with a saturated sodium bicarbonate solution and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThen, the filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by NH silica gel column chromatography (dichloromethane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7cd8e4f6f44d46499f7fe8b1feca0112
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158638B2

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